Both Ends of the Table, Part 4
The Tax Bill Hiding in a Good Year
June 16, 2026
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Show Notes
Eddie and Betty's Conversation
You know, when most people think about getting a windfall, an inheritance or selling a business, they picture the celebration. But there's something hiding in that good news that can turn really expensive if you're not careful. Eddie, Ian Schaeffer wrote about this idea of a tax bill that hides inside what should be a great year. What does he mean by that?
It's one of those things that sounds almost backwards at first. You inherit money, you sell a property, maybe you do a big Roth conversion. Your income jumps way up for that one year, and you think, 'Well sure, I'll pay more taxes, but it's worth it.' What Ian's talking about is how that single spike doesn't just hit you once. It can set off this whole chain reaction of different taxes and surcharges, some of which don't even show up until two years later.
Two years later? That seems like such a random timeline. How does that work?
That's the Medicare piece, and it's the one that catches people completely off guard. Your Medicare premiums, both Part B and Part D, are set based on your income from two years ago. So if you have a big income year today, you won't see the Medicare premium increase until two years from now. And by then, most people have completely forgotten about whatever caused that income spike.
So you're telling me that if I inherit my aunt's retirement account this year and take it all out at once, not only will I pay more taxes this year, but my Medicare premiums could jump in 2027?
Exactly. And here's what makes it worse. According to what Ian wrote, it works like a cliff. So if you go just one dollar over whatever threshold they're looking at, you get hit with the entire surcharge for that level. It's not gradual, it's all or nothing.
That seems really harsh. Can't you appeal it if it was just a one-time thing?
This is where it gets frustrating. Ian points out that these surcharges from windfalls usually can't be appealed, because selling an asset or taking an inheritance isn't considered one of the specific life-changing events that Medicare allows you to use for relief. Once that good year is in the books, you're generally stuck with the surcharge.
Okay, so the Medicare thing happens two years later, but what about all the other taxes? You mentioned there's a whole chain reaction that can happen in that same year.
Right, so in the article Ian breaks down four different taxes that can all stack up at once. The first one is obvious, you get pushed into a higher income tax bracket. The top slice of that windfall gets taxed at a higher rate than your normal income.
That makes sense. What's the second one?
More of your Social Security becomes taxable. A lot of people don't realize that as your other income rises, up to 85 percent of your Social Security benefits can become subject to income tax. Maybe before none of it was getting taxed, and suddenly most of it is.
Wait, I thought Social Security was already something you paid taxes on when you earned it. Why are they taxing it again when you receive it?
It's one of those things where the rules are just different than what feels logical. The way Social Security taxation works, if your total income stays below certain levels, your benefits aren't taxed at all. But as your income rises, more and more of those benefits become taxable. So a big windfall can suddenly make your Social Security benefits part of your tax bill when they weren't before.
Got it. So that's two. What's the third tax that can pile on?
This one's called the 3.8 percent surtax on investment income. Once your modified income passes $200,000 if you're single or $250,000 if you're married, you get hit with an extra 3.8 percent tax on things like interest, dividends, rents, and capital gains.
Those thresholds seem kind of low for today's world. Do they go up with inflation?
No, and that's part of what makes this tricky. Ian mentions that those thresholds never adjust for inflation, so more people cross them every year. What seemed like a high-income problem when the rule was created is catching more and more middle-class families now.
And the fourth tax?
Your capital gains rate can jump from 15 percent up to 20 percent. So if part of your windfall involves selling investments, not only might those gains be subject to the 3.8 percent surtax we just talked about, but the base capital gains rate itself goes up too.
So let me make sure I understand this. In one year, you could have a higher income tax bracket, more of your Social Security getting taxed, this 3.8 percent surtax, higher capital gains rates, and then two years later your Medicare premiums shoot up. That's five different ways the same windfall hits you.
That's exactly right. And Ian's point is that each one might seem modest on its own, but when they all stack together, they can turn what should be a financial blessing into a surprisingly expensive event.
This feels especially relevant for people dealing with inheritances, doesn't it? I mean, that's been the theme of this whole series Ian's been writing.
Absolutely. He specifically calls this out as not being a someday problem for families receiving inheritances, it's their problem right now. A large inherited retirement account is one of the most common triggers because all that money coming out is taxable, and there's that ten-year deadline we've talked about in previous episodes.
Right, so people feel pressured to get the money out quickly, but that pressure can actually cost them a fortune.
Exactly. Ian gives a really clear example. If you pull it all out in one or two years, you can light up every single one of these taxes at the same time, plus that Medicare surcharge two years later. But if you spread the same withdrawals thoughtfully across the available years, you might avoid most of them. He says the difference between those two approaches, on the same inheritance, can be tens of thousands of dollars.
Tens of thousands of dollars just based on timing. That's a huge difference for making the same financial decision, just spread out differently.
And that's why he keeps coming back to this theme of coordination throughout the whole series. The money itself isn't complicated, it's keeping track of all these different rules and thresholds and timelines that's the hard part.
Let's talk about some of these specific thresholds, because I think people would want to know what numbers they should be watching for. You mentioned $200,000 and $250,000 for that investment income surtax.
Right, that's $200,000 for single filers, $250,000 for married couples. But here's the thing, there are different thresholds for different taxes, and some of them are probably different than what people might expect. The exact details of where each one kicks in, I'd want to double-check those specific numbers with our team at American Retirement Advisors rather than guess at them.
That's probably smart. And what about the Medicare premium increases? How much are we talking about when those kick in?
Ian mentions it can be several hundred dollars a month per person. So if you're married, you're both getting hit. And remember, this is happening two years after the income spike, when you've probably forgotten all about what caused it in the first place.
Several hundred dollars a month, that adds up to thousands of dollars a year. And it's not like it phases in gradually?
No, that's what makes it so brutal. Ian emphasizes that it works like a cliff. Going just one dollar over a threshold triggers the entire surcharge for that tier. So you could be $1 over the line and pay the same extra premium as someone who's $10,000 over the line.
That cliff effect seems really unfair. Is there any way to fix it after the fact?
This is the part that I think catches people most off guard. Ian explains that a surcharge caused by a one-time windfall usually can't be appealed. Medicare has specific life-changing events that qualify for relief, but selling an asset or taking an inheritance generally isn't one of them. Once that good year is in the books, the surcharge is typically locked in.
So the key is planning ahead of time, not trying to fix it later.
Exactly. Ian's whole point is that none of this should make you afraid of a windfall, but it should make you want to see it coming and plan around it. And the good news is, it's entirely possible to do that when someone's watching for it.
What does that planning actually look like? I mean, if someone knows they're about to inherit a large IRA or they're thinking about selling their business, what should they be thinking about?
Ian mentions several strategies. Spreading income across years, timing a sale carefully, coordinating withdrawals with your other income, being mindful of the thresholds. The key is that it only works if it's planned in advance by someone who's looking at the whole picture.
Let's get practical for a minute. Say someone inherits a $500,000 IRA and they have that ten-year window to empty it. What's the difference between doing it smart and doing it the expensive way?
Well, the expensive way would be to panic about the ten-year deadline and pull it all out in year one or two. That's $500,000 of extra taxable income all at once. Depending on what their normal income is, that could push them into the highest tax brackets, trigger all these surtaxes, make most of their Social Security taxable, and guarantee those higher Medicare premiums down the road.
And the smart way?
The smart way is to look at their normal income, figure out how much extra they can take each year without crossing these various thresholds, and spread it out accordingly. Maybe it's $50,000 a year for ten years, or maybe it's uneven depending on what else is happening in their financial life. The exact strategy would depend on their specific situation.
That makes sense. What about people who are thinking about doing Roth conversions? This seems like it would apply to them too.
Absolutely. A Roth conversion creates taxable income just like an inheritance withdrawal does. So if you're not careful about the timing and the amounts, you can trigger the same stack of taxes. The difference is, with a conversion you usually have more control over the timing since you're choosing to do it.
Right, nobody's making you do the conversion by a certain deadline.
Exactly. So you have more flexibility to spread it out or time it for years when your other income might be lower. But you still need to be thinking about all these same thresholds and the Medicare lookback.
Let's talk about that Medicare lookback again, because I think that's the piece that would blindside most people. How does someone even find out that their premiums are going up, and when does that happen?
You know, the mechanics of how and when Medicare notifies people about premium increases, I'd want our team to walk through those specific details. But Ian's point is that it happens two years later, and most people have completely forgotten about whatever caused that income spike by then. So they just see this sudden jump in their Medicare costs and have no idea where it came from.
That would be so frustrating. You think you've moved on from dealing with an inheritance or a business sale, and then this surprise bill shows up years later.
And by then it's too late to do anything about it. That's why Ian keeps emphasizing that the time to plan for this is before the big year happens, not at tax time the following spring.
What would that planning conversation actually look like? If someone came to you and said, 'I'm about to inherit my dad's IRA, it's worth about $800,000, what should I be thinking about?'
First thing would be to map out their current income and tax situation. What tax bracket are they in normally? Are they already taking Social Security? Are they close to any of these thresholds we've been talking about? Then we'd look at the ten-year timeline and figure out how to spread those withdrawals to minimize the total tax impact.
And the Medicare piece?
We'd want to model out what their Medicare premiums would look like in two years based on different withdrawal strategies. Maybe taking an extra $30,000 this year versus next year makes no difference to their current taxes, but it could mean hundreds of dollars a month in Medicare premiums down the road.
It really is all connected, isn't it? You can't just look at one piece of it.
That's exactly Ian's point about coordination being more important than returns once you have real wealth. It's not about finding the perfect investment, it's about making sure all these different rules and timelines work together instead of against each other.
What about people who have already had their big year? Is there anything they can do now, or are they just stuck waiting to see what happens to their Medicare premiums?
If the big year already happened, there's not much you can do about that specific year's impact. But you can make sure you're planning better for any future windfalls or large income years. And you can at least know to expect the Medicare premium increase so it doesn't come as a complete shock.
That's something, I suppose. At least you can budget for it.
Right. And this is exactly the kind of thing that Ian mentions they map out in those Inheritance Planning meetings. You're coordinating the withdrawals, the thresholds, and that two-year Medicare lookback so a good year stays a good year.
Before we wrap up, I want to make sure people understand that this isn't a reason to be afraid of good financial news. An inheritance or selling a business successfully, these are good problems to have.
Absolutely. Ian makes that point clearly. None of this is a reason to fear a windfall. It's just a reason to see it coming and plan around it. The difference between doing it thoughtfully and doing it haphazardly can be tens of thousands of dollars, but both ways you still got the windfall.
And the planning part is very doable?
Ian says it's very doable with a little foresight. It's not about avoiding the income, it's about being smart with the timing and understanding how all these different pieces fit together.
This has been such an important conversation. I think a lot of families are going to recognize themselves in this situation, either now or in the future. The key takeaway seems to be that timing matters enormously, and the best time to plan is before that big year happens, not after. If you're facing an inheritance, thinking about a Roth conversion, or considering selling a business or property, this is exactly the kind of situation where sitting down with someone who can see the whole picture makes a real difference. You can reach our team at American Retirement Advisors at 602-281-3898 to talk through your specific situation. Don't let a good year accidentally become an expensive year when a little planning could have made all the difference.